


A Date Night With Lenny

by Anboringday



Series: An Outlaw's Sexapades [3]
Category: Red Dead Redemption (Video Games)
Genre: F/M, Fluff, Kinktober 2020, Kissing in the Rain, Plot What Plot/Porn Without Plot, Slow Dancing, Smut, getting laid by the cutest cowboy ever
Language: English
Status: Completed
Published: 2020-10-12
Updated: 2020-10-12
Packaged: 2021-03-07 23:21:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,941
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26962060
Author URL: https://archiveofourown.org/users/Anboringday/pseuds/Anboringday
Summary: Edging Kink: engaging in sexual stimulation to the point of ejaculation before stopping and starting again.Lenny and his lover spend some quality time at the saloon. Head over heels for one another, it isn't long before things get hot and heavy...
Relationships: Leonard "Lenny" Summers/Original Female Character(s), Leonard "Lenny" Summers/Reader
Series: An Outlaw's Sexapades [3]
Series URL: https://archiveofourown.org/series/1960180
Kudos: 15





	A Date Night With Lenny

**Author's Note:**

> A little something I wrote for kinktober...enjoy!

Arms linked, Lenny and I sauntered out of the crowded saloon. It was a lively night in Valentine, a constant stream of interested visitors trotted through on horseback. Fellers loitered outside the stores, laughing and chatting boisterously. Penned pigs squealed, stray dogs panted in the heat, and chimes rung as doors opened. The noise and activity of the teeming little town was disorderly and loud, but not unpleasant. In fact, it was quaint. The people here were unfettered, spirited, and unapologetically free. 

Normally, I felt rather small and out of place in the company of strangers, but with Lenny beside me, all my silly fears and insecurities melted away. He escorted me through town in his black brushed cotton vest and matching trousers, his shirt and neckerchief both a pristine white. And _god_ , he looked damn fine too, putting every other man in attendance to shame. Ever so often, the women that crossed our path would stare, sometimes tripping over their own feet as they took in his remarkably handsome face.

But he was all _mine_ , and I made it known to the world by keeping my arm hooked possessively around his. Occasionally rubbing his strong shoulders. Stroking his toned biceps. He’d return the affection by showering my cheeks with tiny, playful kisses as we strolled aimlessly along Valentine’s dirt road. We had no destination in mind, no grand plans, or schedules to keep. We were simply enjoying each other’s company, and I couldn’t have been happier.

Cradling a flask of whiskey to his chest, Lenny took a swig. “See, the saloon wasn’t so bad, right? We ate a full course, top-notch quality meal in absolute peace, undisturbed—no bar fights, and only a few drunken bastards got rowdy and ruined the mood. Usually it’s much worse.”

“We have to keep a low profile,” I muttered. “We’re lucky no one recognized you.”

“Have you forgotten that I am _the_ living embodiment of luck—” He tripped over a rock and tumbled clumsily, landing on his backside with a rough _thud_.

My heart skipped a beat. “Lenny!” I hovered over him. “Are you okay?”

With the cutest, goofy grin plastered to his face, he patted himself down for injuries. “No broken bones…I’ll live, I reckon.” 

His wide, bright smile was contagious. Holding the hem of my flowy skirt, I crouched to his level and surveyed him briefly. Besides being stricken with a bad case of the giggles, he seemed fine. “Of course, you’ll live. You have an obligation to keep breathing, Mr. Summers, ‘cause I wouldn’t last a day without you.”

“Is that so? I guess you’re stuck with me then… _forever!_ ” His arms enclosed around my waist, he tugged me to the ground playfully.

“Get off, you silly man!” With a hastily suppressed snicker, I squirmed about in his warm embrace. “Release me!”

“Nooo, you can’t get rid of me—not _ever!_ You’re all mine. Just submit already, woman!” He attacked my cheeks with a frantic rush of kisses.

I smothered a chuckle from the sensation of his beard stubble brushing against my skin, but once he started tickling my sides, my voice rang up a scale and crackled hysterically. Whenever I tried to pull away, he’d draw me right back in, fragrantly fun, carefree, and mischievous despite the dozens of onlookers in our midst.

I tickled him back, and Lenny’s laughter was so jubilant, pure as the Heavens above, childish even despite his adulthood and masculinity. His mirth was like the summer sun and the stars at the peak of dawn. Whenever I heard it, no matter the time of day or weather, the world brightened.

Breathing in his tantalizing, uniquely familiar scent, I nuzzled my nose against his. “ _I love you_.”

Stiffening abruptly, a rush of red stained his cheeks. His voice lowered, quiet and shy. “Hey, you’re making me feel all fuzzy and warm inside. There’s folks around—I’m not blushing, am I?”

“You are. It’s adorable.” I stood and extended a hand to him. “Now get up outta that dirt, silly.”

“C’mere, Sugar.” With a captivating smile, he lured me down to his level once again. He tipped his chin toward the sky. “Look at the stars, ain’t they pretty?”

Pinpoints of silver peeped in and out of the masses of gray clouds overhead. It was going to rain soon. I wiped the dust from my skirt. “You’re ruining my outfit, handsome.”

“What does it matter? I’m just gonna take it off you anyway.” He took another sip of his whiskey.

“I think you’ve had too much to drink, cowboy.”

Music blared from the nearby saloon, a live performance it sounded like. There was clapping and cheering, a soulful feminine voice filled the air, blending in elegantly with the strum of stringed instruments.

Lenny’s brows shot up. “You hear that?”

I nodded. “It sounds lovely.”

He tossed his whiskey aside and rose, lifting me along with him. Taking my hand in his, he preformed a courtly bow, pressing a kiss to my knuckles. “My lady, may I have this dance?”

“Dance?” My face heated at the proposal. “H-here?”

“Right here, right now.”

Filled with embarrassed discomfort, I lowered my head. “There’s an awful lot of people around, Lenny.”

“Don’t be scared. We’re in this together. Just focus on me, okay?”

Arms encircling my waist, he anchored me against him, swaying to the music. I was tense and on edge at first, I’ve never danced in public. Let alone in the center of town where just about every neighboring feller, woman, loyal steed, and child could take a gander.

But once his hazel gaze found mine, our bustling surroundings melted away. Hypnotized by the shimmering sparks of gold in the depths of his eyes, all I could see was him. The way his lean body glided with effortless rhythm and fluidity. How his muscles flexed and rippled with every slight movement beneath his shirt. Following his gentle motion, my arms slid around his neck. He was my world, and the moment was ours.

“We coulda done this _in_ the saloon, you know,” I said.

“Maybe,” he mumbled. “I know going to that saloon in particular was my idea, but uh, honestly…I didn’t feel comfortable in there.”

“Why? Did one of those drunkards do something? Say something? I swear, if there are any inbred yokels around here, you just point me in their direction—”

“No, it wasn’t that.” He gave a shaky laugh. “Every fella in there was eyeballing you. It ain’t no crime to look but…” His voice trailed off.

I frowned. “I didn’t notice anyone was staring, I’m sorry—”

“Hey, don’t apologize for being the prettiest girl in town. You got all the women in the West green with envy and the fellas? They salivate over you like a pack of rabid dogs after a bone. And regardless of all that, you chose me. Feels like a dream. The best damn dream.” He dipped me back and kissed my temple. I held onto him as his full lips drifted to my neck, brushing over my sensitive skin. I closed my eyes on a moan when he caught the lobe of my ear between his teeth, the spontaneity of it all warmed my heart, and awakened a fierce ache between my legs.

With he straightened me, I was near breathless and dizzy. There was an applause, and whistling coming from over my shoulder. Lenny’s grasp on me was strong and clinging, as if I could slip through his fingers at any given moment. “You’re mine, I’m yours, and now everybody knows it.”

I flushed, perversely flattered and delighted by his possessiveness. “You know, this isn’t exactly what I’d call ‘keeping a low profile’,” I whispered.

“So, about that…” He grinned sheepishly, a boyish smile so cutely at odds with the wiry, solid sexuality of his body. “I ain’t the best at laying low, never have been. Everywhere I go, something or somebody starts kickin’ up a fuss and I get dragged into it. For example, some fool gets robbed—by no fault of mine, might I add—then that same fool gets brave and winds up with a bullet in his gut. And of course, being the law-abiding citizen that I very much am, I got no choice but to intervene.”

I smiled. “So, all this time you’ve been playing the hero? Everything the lawmen said about you was a lie?”

“The law ain’t never been fair or smart.”

“That much is true.” The sky rumbled, and the clouds began to shed some heavy droplets of rain. Folks began to retreat indoors, while a select few preferred to take shelter under the general store awnings.

“Well, there goes our audience,” Lenny said. “A real shame, too. I was getting used to the limelight.” He took off his brown leather cowboy hat and gave it to me. “Here, Sugar. For your hair.”

“Thank you.” I nuzzled my face to his chest. “We should go. The storm is only going to get worse.”

Seemingly unbothered by the rain, he tilted my chin up and settled his mouth on mine. A rush of warmth flowed through me, the soft sweetness of his kiss weakened my knees. Gradually, the pressure of his lips increased, and I surrendered myself to him. His tongue stroked slow and tenderly over mine. Our connection was wildly passionate and undeniable. I was so absorbed by him, possessed by his sweet love, I hardly noticed the drizzle running down our faces to where our lips connected. The cold rain mingled with the uniquely wonderful taste of him.

The working of his mouth against mine made me hot. Restless. I pushed a hand into his gloriously damp hair and sucked on the bottom of his lip, tracing my tongue over its perfect fullness, nibbling, gently pulling…

The sound of his groan was so satisfyingly deep and erotic, my core throbbed, uncomfortably wet. Lenny broke the kiss, his chest heaving. “ _Damn…_ what are you doing to me?”

I smiled innocently. “I have no idea what you’re talking about.”

Gripping my hips, he crushed me to him, the impressive package between his legs brushed my thigh. “I…I-I need to be inside you,” he confessed with some difficulty. “I’m aching.”

Moved by the extent of his longing, I stood on the tip of my toes and reclaimed his lips, my palms sliding all over his lethally sexy body. We were drenched in the chilly, pouring rain, but not even the forces of nature could keep my hands off him. “There’s a hotel next door,” I said between kisses.

Lenny nodded an assent and lifted me off my feet, my legs hooked around his waist. He carried me across the road and through the hotel’s swinging doors. The lobby was empty.

“I’ll be just a minute!” a voice I presumed to be the receptionist called out from down the hall.

Still holding me in his powerful arms, Lenny leaned against the front desk as we made out with reckless abandon. The soul-reaching massage of his lips sent shivers rippling up my spine. Raising my skirt a fraction, his hips started moving, the hard length of his cock grinding sinfully against me through the confides of his pants. _Oh, god…_ a deep hunger stirred inside me. I _had_ to have him—all of him—and it _had_ to be soon. Or else I’d go crazy.

I held onto him for dear life, trembling from the hot, delicious friction. I didn’t care who was watching. I was way past the point of shyness, the primal desire to be fucked by this beautiful outlaw was at the forefront of my mind. It was all that mattered.

My skin burning hot and flustered, I whimpered. “I want you, Lenny.”

Muscles tense and visibly shaking with lust, he uttered huskily, “Fuck, I want—I _need_ you.”

I buried my face in the crook of his corded neck, ravaging his skin with love bites and licks. “How bad do you need me?”

“Real bad. More than anything. I’ll beg if I got to. I’ll plead. I’ll get on my damn knees right now.” He swallowed deep, his expression tight and eyes smoldering. “If we don’t get a key soon, I might just bend you over this desk and fuck you right here.”

I trembled. It sounded like a threat as much as a promise, the scorching intensity of his words so unlike him. He was losing his composure, the desire stripping away his inhibitions and calm, sweet-tempered mannerisms. Only I could do this to him. It was a major turn-on and confidence boost.

“Here I am!” the receptionist finally arrived, scrambling into his rightful place behind the desk. His presence was a blur, I was too preoccupied enjoying the softness of Lenny’s lips. I could probably come like this, just by kissing him if we went at it long enough.

“Good Lord Almighty!” the receptionist gaped at us. “You kids need a room immediately! Luckily for you, we have one available. Just one. It’s been a big night for tourism, with that band of fancy folk from Saint Denis parading through town, playing their music and causing a ruckus. I don’t understand how anyone can get anything done with all that darn noise and commotion—”

Lenny shoved a hand into his satchel and flung a couple dollars at the chatty receptionist. It stopped his ranting, thank goodness.

“Second floor, first room on your right.” Once he passed over the key, Lenny whisked me upstairs. Heedless of everything and everyone, our hot, lingering kisses didn’t break as he fumbled with the lock. A moment later, the door opened, and we were inside a dimly lit room bathed in candlelight, rain softly drummed against the windowpanes.

Lenny dropped me on the bed. I reached for his vest and ripped it open, the buttons scattered across the hardwood floor. “Get naked, cowboy.”

He laughed, shrugging out of his shirt and suspenders, and then unbuckling his gun belt. I ran my hand down his chest in awe. His deep brown skin illuminated by the warm, flickering light, he glowed like flames piercing the darkness, radiant with transcendental beauty and mystery. I wanted him so bad, it hurt.

I nuzzled my face against the solid ridges of his damp, god-like abdomen. “Christ, why are you so perfect?”

“Perfect?” He pinched my cheek playfully. “ _Aw_ , you really think so? Arthur told me the same thing once, but he was drunk and vomiting in a pig pen outside the saloon when he said it—”

“Lenny…” Grinning, I swatted his hand off my cheek. “You’re ruining the mood.”

“Oh. Right. Sorry.” Flashing an apologetic smile, he tossed aside the wet hat on my head and helped me out my clothes with gentle finesse. I went for his zipper, freeing his thick cock. My mouth watered. He was rock-hard, and throbbing. I traced the flat of my tongue along the heavy veins coursing his length, slow and worshipfully. 

He fisted my hair, restraining me _just_ before I took him into my mouth. “Nuh-uh, Sugar. That can wait. Lay down.”

My brows raised. Apparently, Lenny was in charge tonight. I obeyed, curious of what he had in store.

The heat and clean, woodsy scent of his body took my breath away once he came down on me. “You’re beautiful.” He plumped one breast in his hand, kissing my neck, his lips grazing back and forth over my tender, flustered skin. I squirmed from the heady sensation. My legs locked around his hips, silently urging him to make love to me already. Near mindless with need, I struggled to find my voice, to formulate words. All that slipped from my throat was tiny, helpless whimpering.

He took himself in his hand and stroked my slick entrance, the soft nudges of his cock head agonizingly teasing. I arched my hips, my body straining toward him, desperate for a connection. He was making me wait, avoiding my clit and somehow resisting the temptation of fucking me despite my pleading.

“Lenny, please. What are you waiting for?”

“Hush now,” he said. “You’ll be ready for me soon.”

“I’ve been ready for you for the longest. Since this morning.”

He nipped my neck, sucking feverishly. Surely leaving a mark behind. Inflamed and trembling in distress, I rolled my hips against the rigid column of flesh he so cruelly teased me with. Patiently, he coaxed me to the brink of insanity. I was soaked in my own wetness, creaming madly for the feel of him inside me.

Raking my nails across his back, I pulled him closer. I needed him to fuck me more than I needed my next breath. “Now,” I gasped. “Need you _now_.”

With an expert shift of his hips, he pushed into me hard, and so pleasantly deep.

“Oh, God, yes,” I moaned, shuddering, clenching around him. _Finally._ Warmth struck my heart. I’ve been waiting for this for so long, too long—

“Don’t come,” he murmured, his palms slipped under my hips and cupped my behind, squeezing.

“ _Excuse me?"_ I was so close to the edge already. How the hell did he expect me not to go off?

“Good things come to those who wait. It feels so much better in the end.” Lenny started to move, his thrusts lazy and tortuously slow. “Can you do that for me, Sugar? Can you make it last?”

The cadence of his soft-spoken, drawling words sounded so sweet in my ears, so delicate. A fierce ache struck my chest. I was hopelessly in love with him, and more than willing to submit to his every need and request.

“It’s not fair,” I mumbled, my vision blurred with tears. “You have no idea how good you feel inside me.”

“Trust me, I-I do.” Lenny’s leisurely rhythm came to an abrupt halt, his body shivered violently. Jaw clenched, a groan slipped through his lips, tension contorted the gorgeous features of his face. Holding back seemed to be affecting him as well.

Quickly regaining his poise, he resumed screwing me. Lenny knew my body so well, all the tender spots that demanded attention and how precisely to stroke them. It was all muscle memory to him at this point. Over and over, his cock rubbed the bundle of quivering nerves clenching, aching for his touch.

Gripping the sheets with white-knuckled force, I smothered an upsurge of sobs, thrashing against the overwhelming need to climax. I was burning from the inside out, our bodies sticky with sweat. Trembling uncontrollably, I couldn’t hold back for much longer…

“Don’t come,” Lenny repeated. “Make this last. Just hold on.”

“I c-can’t. It feels amazing. Jesus, Lenny…” Tears escaped my eyes. I was falling apart, utterly and irreversibly lost in him. “ _I love you. I-I love you so, so much…_ ”

He kissed away the tear tracks on my face. “Hold me. Don’t you let go.”

I released the covers and clung to him. His heavy-lidded gaze snagged with mine, searing into me. He sighed heavily, from pleasure, tension, or both—I couldn’t tell. His hips still surging at a moderate, deliberately restrained tempo that was driving senseless, I blurted, “Slow down. Please. I’ll come if you don’t slow down.”

“Will you now?” A wicked smile pulled at his lips. “I thought you wanted to come, Sugar. Why the change of heart?”

My back arched as his hold on my behind grew bruising. He lifted my hips into his thrusts, and I cried out, my core boiling and tightening with a pressure so severe, I feared I’d snap in two if I didn’t give into my bodily cravings soon.

“I won’t come,” I panted. “Not—not until y-you say so.”

His hazel eyes softened, sympathetic almost as he watched me quiver helplessly beneath him. One hand clasping the side of my face, he kissed me with a heartrending tenderness, his tongue caressing mine. _Yes._

“Come for me,” he fucked me harder, dominating my body, although his voice was honeysweet against my lips. “I need to feel you…”

With his permission, an orgasm erupted inside me like a volcano, molten pleasure spreading from my core and overcoming the entirety of my body in a scorching wave. It was remarkable. Explosive. Unlike anything I’ve ever felt before. I let out a shrill cry, writhing under Lenny’s sweat-slick muscles. His name spewed repeatedly from my lips as he fucked me into blissful oblivion.

The climax surged on and on. I was melting, drowning in the immense ecstasy of being loved by him, pleased by him. He was my everything, and without him I was empty and hollow. I could die in his arms right now and regret not a thing, because I’ve never truly lived a day until I met him. 

The connection we shared was incredibly intense, inside and outside the bedroom. But when we were making love like this, intimately linked, giving and receiving pleasure from one another like our lives depended on it…our bond felt unbreakable. It was frightening how deeply I adored him—an outlaw. A man the law wanted strung up by a noose…

A muscle twitching in his jaw, he rode out my climax until the clenches faded; then he slowed down his pace, burying himself inside me languidly. He sucked in a harsh breath, eyes dark and dilated, his strong body convulsed furiously. He was teetering on the edge of an orgasm, still denying himself the pleasure he’s been working toward all night long. The glaring self-control and perseverance Lenny emanated was something to be envied.

I gathered his hair in my hands, kissing the side of his damp throat. “You’re shaking, handsome. Do I feel _that_ good?”

“ _Yes_ ,” he rasped, pounding into me erratically, his balls slapping against the curve of my behind. “Oh shit, _yes_.”

A bead of sweat dripped from his chin onto the corner of my lip. I slid my tongue along his sculpted jawline, collecting the saltiness with a soft murmur of satisfaction. He tasted so good, and the scent of his lust smelled even better.

“Why don’t you come inside me, cowboy?” I teased, my voice husky. “You know you want to.”

He clasped the nape of my neck, his gaze burned into mine. “Do _you_ want me to?”

I had just as much control over his body as he did mine and I couldn’t help but smile. “Yes, Lenny. Come.”

With a serrated groan, his beautiful cock jerked, spurting hotly, flooding me with his heat. His hips ground against mine, he emptied his load as deeply as he could inside me. I don’t know how long we laid there holding each other, spent and panting. Eventually, our breathing steadied and our bodies cooled.

“Leonard Summers!” a rugged voice shouted from outside, piercing the calm serenity of the rain. “We know you’re in here! Give yourself up, boy, there ain’t nowhere left to run!”

Lenny shot up from the bed.

Still wrapped up in a sex-induced daze, my brain struggled to comprehend what the hell was happening. Lazily, I sat up, covering my exposed breasts with the sheets. “What’s going on?”

Lenny inched to the window and glanced furtively though the blinds. “Lawmen,” he winced. “A lot of ‘em.”

I shivered, my heartbeat sped up. “You’re joking. Please tell me you’re joking.”

“I wish I was, Sugar. Maybe you were right—coming ‘round here was, in fact, a real bad idea.” His teeth gleamed in a lopsided smile, confident and reassuring despite our unfortunate circumstances. “So, uh…you know how to handle a gun, right?”

My eyes widened. _Oh no…_

**Author's Note:**

> Thanks for reading guys! Follow Anboringday on tumblr for rdr fanart or if you just wanna talk! Requests are open!


End file.
